The present disclosure relates to methods of making poly(octatriazacane) materials.
New polymer-forming reactions are difficult to design due to strict requirements for efficient, straight-forward, and clean chemistry. Small molecule octatriazacanes have been synthesized previously but have never been explored as a potential polymer-forming reaction. A new and simple polymer forming polycondensation of diamines with paraformaldehyde to poly(hexahydrotriazine)s and poly(hemiaminal)s has been previously described.

These poly(hexahydrotriazine)s exhibited high Young's modulus (˜14.0 GPa for the freestanding films) but are completely amorphous and generally lack free volume within their polymer matrix due to their high crosslink density. Additionally, these polymers suffer from poor yield strength and solubility and electron-deficient monomers do not react to form polymer according to this reaction scheme. Therefore, polymers that are structurally similar to the poly(hexahydrotriazine)s and poly(hemiaminal)s but having improved yield strength and solubility and which might incorporate electron-deficient monomers would be of interest.
A need exists for methods of making new polymers having improved properties and better performance in the areas described above.